— 178 — 



oxime of «-pinene (I), or upon a solution of this body in the calculated 

 quantity of dilute acid, the result, according to a communication by 

 G. Cusmano 1 ) is an almost quantitative yield of «-pinene-isonitramine 

 oxime (II or VI), a compound melting at 127° (with decomposition) and 

 occurring in the form of colourless prisms. The hydroxylamine salt is 

 formed when equimolecular quantities of isonitramine oxime and hydroxyl- 

 amine are mixed in alcoholic solution; it forms prismatic crystals, m. p. 110° 

 (with decomposition). When «-pinene-isonitramine oxime, suspended in 

 water, is heated on the water-bath, almost the calculated quantity of 

 nitrous oxide is split off, and hydroxy-dihydrocarvoxime (III) is formed. 

 The same reaction takes place when the body is heated with 20°/o aqueous 

 acetic acid. The sodium salt of the isonitr amine oxime when heated in an 

 aqueous-alcoholic solution splits off nitrous oxide and yields nitrosopinene 

 (IV) and small quantities of o-hydroxypinocamphone oxime (pinene hydrate 

 oxime) m. p. 128° (V). The last-named compound, when heated with con- 

 centrated oxalic acid, yields hydroxydihydro - carvoxime. o-Hydroxypino- 

 camphone oxime is probably formed also primarily by the action of dilute 

 acids upon the isonitvamine oxime; in wnich process the latter substance 

 probably reacts in the manner set forth in formula VI. 



1 



HON:C 



i 3 CC(NHOH) 



/\ 



HhC-c-chJ 



1 

 HON:C 



i 3 CC(N 2 C 



H3C • C • CH3 



) 2 H) 

 CH 



HON:C 



CCH 



•CH 



H 2 Cx 



JCH 2 



H 2 C 



\ 





CH 2 



H 2 C 



x /CH 2 



C 



H 



\ 

 C 



H 





C 



I. 



II. 



(CH 3 ) 2 C(OH) 

 III. 



CCH 3 



H 3 CCOH 



/\ 



H 3 C N:NOH 



X 6 



HON:(X ^> 



C 



HON:C 



/ \ 



CH 



HON:C 



{., ^>CH 





H 3 C-C-CH 3 







H 3 C-C-CH 3 







H 3 C * C* CH 3 





H 2 Cx 



C 



/CH 2 

 ti 



H 2 C 



C 



H 



CH 2 



H 2 C 



c 



H 



CH 2 



F 



/. 







> 



f. 







\ 



ti. 





x ) Atti R. Accad. dei Lincei, Rome (5) 19 (1910), I. 747; quoted from Chem. Zentralbl. 

 1910, II. 388. 



